Extremely strong and readily accessible AAA-DDD triple hydrogen bond complexes

Journal of the American Chemical Society

Volumn 129, Issue 3, 2007, Pages 476-477

  Djurdjevic, Smilja ^a   Leigh, David A ^a   McNab, Hamish ^a   Parsons, Simon ^a   Teobaldi, Gilberto ^a   Zerbetto, Francesco ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; CYCLIZATION; FLUORESCENCE; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

CHLOROFORM; CRYSTALLOGRAPHY, X-RAY; DEUTERIUM; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE;

EID: 33846446063     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067410t     Document Type: Article

References (22)

1. (a) Zimmerman, S. C.; Corbin, P. S. Struct. Bonding (Berlin) 2000, 96, 63-94.
2. (b) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097.
3. (c) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2383-2426.
4. (d) Schmuck, C.; Wienand, W. Angew. Chem., Int. Ed. 2001, 40, 4363- 4369.
5. (e) Sherrington, D. C.; Taskinen, K. A. Chem. Soc. Rev. 2001, 30, 83-93.
6. (f) Sijbesma, R. P.; Meijer, E. W. Chem. Commun. 2003, 5-16.
7. (g) Zimmerman, S. C.; Park, T. Polym. Prepr. 2005, 42, 1159-1160.
8. (a) Jorgensen, W. L.; Pranata, J. J. Am. Chem. Soc. 1990, 112, 2008-2010.
9. (b) Pranata, J.; Wierschke, S. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1991, 113, 2810-2819.
10. (a) Murray, T. J.; Zimmerman, S. C. J. Am. Chem. Soc. 1992, 114, 4010-4011.
11. (b) Zimmerman, S. C.; Murray, T. J. Tetrahedron Lett. 1994, 35, 4077-4080.
12. The reductive instability of 1 can also be overcome by using a protonated 2,6-aminopyridine derivative as the DDD partner. See: Bell, D. A.; Anslyn, E. V. Tetrahedron 1995, 51, 7161-7172.
13. (a) Sugiyama, Y.; Adachi, K.; Kawata, S.; Kumagai, H.; Inoue, K.; Katada, M.; Kitagawa, S. CrystEngComm 2000, 2, 174-176.
14. (b) Sugiyama, Y.; Adachi, K.; Kabir, M. K.; Kitagawa, S.; Suzuki, T.; Kaizaki, S.; Kawata, S. Mol. Cryst. Liq. Cryst. 2002, 379, 419-424.
15. (c) Adachi, K.; Sugiyama, Y.; Yoneda, K.; Yamada, K.; Nozaki, K.; Fuyuhiro, A.; Kawata, S. Chem.-Eur. J. 2005, 11, 6616-6628.
16. Compound 2 was prepared according to Murray, T. J.; Zimmerman, S. C. Tetrahedron 1995, 51, 635-648.
17. Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley-Interscience: New York, 1987.
18. -1 range, GAs-Fit gave similar results to the widely used binding constant determination program available from H.-J. Schneider's group (www.uni-saarland.de/fak8/schneider/Links/download.html).
19. Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310-5324.
20. There is no evidence of deprotonation of 5 by 3 in the UV/vis spectra.
21. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
22. Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1987, 109, 5035-5036.